ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
expand_more
expand_more
format_list_bulleted
Question
Chapter 22.5, Problem 38ATS
Interpretation Introduction
Interpretation:
To draw the product when 1,4-dibromobutane undergoes malonic ester synthesis
Concept introduction:
Malonic ester synthesis is a process in which an halide is converted to a
Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (intramolecular malonic ester synthesis)
Steps involved in malonic ester synthesis are,
- Deprotonation of
- Alkylation of enolate
- Hydrolysis of ester using aqueous acid
- Decarboxylation at high temperature
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Part VII. The H-NMR of a compound with molecular formula C5 H 10 O2 is given below.
Find the following:
(a) The no. of protons corresponding to each signal in the spectra
(6) Give the structure of the compound and assign the signals to each
proton in the compound.
a
70.2
Integration Values
C5H10O2
b
47.7
C
46.5
d
69.5
3.6 3.5
3.4 3.3 3.2 3.1 3.0
2.9 2.8
2.7
2.6 2.5
2.4 2.3 2.2 2.1 2.0
Chemical Shift (ppm)
1.9
1.8
1.7 1.6
1.5
1.4 1.3 1.2
1.1 1.0
0.9 0.8
Part 111. 1 H-NMR spectrum of a compound with integration values in red is given below.
Answer the following:
(a) write the signals in the 'H-NMR spectrum to the corresponding protons on the structure
of the molecule below.
(b) Identify the theoretical multiplicities for each proton in the compound. Also give the possible.
complex splitting patterns assuming J values are not similar.
там
Br
22
2
3
6
4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0
Chemical Shift (ppm)
ra.
Br
2
3
6
6
2.5
2.4
2.3
2.2
2.1
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.1
1.0
0.9
0.8
Chemical Shift (ppm)
2
2
Br
7.3
7.2
7.1
7.0 6.9
6.7 6.6 6.5
6.4
6.3
6.2
6.1
6.0
Chemical Shift (ppm)
5.9
5.8 5.7
5.5 5.4 5.3 5.2
5.0 4.9
1600°
1538°C
1493°C
In the diagram, the letter L indicates
that it is a liquid. Indicate its
components in the upper region
where only L is indicated.
The
iron-iron carbide phase
diagram.
Temperature (°C)
1400
8
1394°C
y+L
1200
2.14
y, Austenite
10000
912°C
800a
0.76
0.022
600
400
(Fe)
a, Ferrite
Composition (at% C)
15
1147°C
a + Fe3C
2
3
Composition (wt% C)
L
2500
4.30
2000
y + Fe3C
727°C
1500
Cementite (Fe3C)
1000
4
5
6
6.70
Temperature (°F)
Chapter 22 Solutions
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
Ch. 22.1 - Prob. 1CCCh. 22.1 - Prob. 2CCCh. 22.1 - Prob. 3CCCh. 22.1 - Prob. 1LTSCh. 22.1 - Prob. 4PTSCh. 22.1 - Prob. 5ATSCh. 22.1 - Prob. 6CCCh. 22.1 - Prob. 7CCCh. 22.1 - Prob. 8CCCh. 22.2 - Prob. 9CC
Ch. 22.2 - Prob. 10CCCh. 22.2 - Prob. 11CCCh. 22.2 - Prob. 12CCCh. 22.2 - Prob. 13CCCh. 22.2 - Prob. 14CCCh. 22.3 - Prob. 2LTSCh. 22.3 - Prob. 15PTSCh. 22.3 - Prob. 16PTSCh. 22.3 - Prob. 17ATSCh. 22.3 - Prob. 18ATSCh. 22.3 - Prob. 19ATSCh. 22.3 - Prob. 3LTSCh. 22.3 - Prob. 20PTSCh. 22.3 - Prob. 21ATSCh. 22.3 - Prob. 22ATSCh. 22.3 - Prob. 4LTSCh. 22.3 - Prob. 23PTSCh. 22.3 - Prob. 24ATSCh. 22.3 - Prob. 25CCCh. 22.3 - Prob. 26CCCh. 22.3 - Prob. 27CCCh. 22.4 - Prob. 28CCCh. 22.4 - Prob. 29CCCh. 22.4 - Prob. 30CCCh. 22.4 - Prob. 31CCCh. 22.4 - Prob. 32CCCh. 22.5 - Prob. 33CCCh. 22.5 - Prob. 34CCCh. 22.5 - Prob. 5LTSCh. 22.5 - Prob. 35PTSCh. 22.5 - Prob. 36ATSCh. 22.5 - Prob. 37ATSCh. 22.5 - Prob. 38ATSCh. 22.5 - Prob. 6LTSCh. 22.5 - Prob. 39PTSCh. 22.5 - Prob. 40ATSCh. 22.5 - Prob. 41ATSCh. 22.5 - Prob. 42ATSCh. 22.5 - Prob. 43ATSCh. 22.6 - Prob. 44CCCh. 22.6 - Prob. 45CCCh. 22.6 - Prob. 46CCCh. 22.6 - Prob. 7LTSCh. 22.6 - Prob. 47PTSCh. 22.6 - Prob. 48ATSCh. 22.6 - Prob. 49CCCh. 22.6 - Prob. 50CCCh. 22.7 - Prob. 8LTSCh. 22.7 - Prob. 51PTSCh. 22.7 - Prob. 52PTSCh. 22.7 - Prob. 53ATSCh. 22.7 - Prob. 9LTSCh. 22.7 - Prob. 54PTSCh. 22.7 - Prob. 55ATSCh. 22.7 - Prob. 56ATSCh. 22 - Prob. 57PPCh. 22 - Prob. 58PPCh. 22 - Prob. 59PPCh. 22 - Prob. 60PPCh. 22 - Prob. 61PPCh. 22 - Prob. 62PPCh. 22 - Prob. 63PPCh. 22 - Prob. 64PPCh. 22 - Prob. 65PPCh. 22 - Prob. 66PPCh. 22 - Prob. 67PPCh. 22 - Prob. 68PPCh. 22 - Prob. 69PPCh. 22 - Prob. 70PPCh. 22 - Prob. 71PPCh. 22 - Prob. 72PPCh. 22 - Prob. 73PPCh. 22 - Prob. 74PPCh. 22 - Prob. 75PPCh. 22 - Prob. 76PPCh. 22 - Prob. 77PPCh. 22 - Prob. 78PPCh. 22 - Prob. 79PPCh. 22 - Prob. 80PPCh. 22 - Prob. 81PPCh. 22 - Prob. 82PPCh. 22 - Prob. 83PPCh. 22 - Prob. 84PPCh. 22 - Prob. 85PPCh. 22 - Prob. 86PPCh. 22 - Prob. 87PPCh. 22 - Prob. 88PPCh. 22 - Prob. 89PPCh. 22 - Prob. 90PPCh. 22 - Prob. 91PPCh. 22 - Prob. 92PPCh. 22 - Prob. 93PPCh. 22 - Prob. 94PPCh. 22 - Prob. 95PPCh. 22 - Prob. 96PPCh. 22 - Prob. 97PPCh. 22 - Prob. 98PPCh. 22 - Prob. 99PPCh. 22 - Prob. 100IPCh. 22 - Prob. 101IPCh. 22 - Prob. 102IPCh. 22 - Prob. 103IPCh. 22 - Prob. 104IPCh. 22 - Prob. 105IPCh. 22 - Prob. 106IPCh. 22 - Prob. 107IPCh. 22 - Prob. 108IPCh. 22 - Prob. 109IPCh. 22 - Prob. 110IPCh. 22 - Prob. 111IPCh. 22 - Prob. 112IP
Knowledge Booster
Similar questions
- Nonearrow_forwardPart II. Given below are the 'H-NMR spectrum at 300 MHz in CDC13 and mass spectrum using electron ionization of compound Brian. The FTIR of the said compound showed a strong peak at 1710 cm"). Determine the following: (a) molecular Formula and Degree of unsaturation of compound Brian (b) Basing on the given H-NMR spectrum tabulate the following (i) chemical shifts (ii) integration, ciii) multiplicity and (iv) interferences made for each signal (c) Draw the structure of compound Brian. ) ΕΙ 43 41 27 71 114 (M+) Hmmm 20 30 40 50 60 70 80 90 100 110 120 1H NMR spectrum 300 MHz in CDCl3 2.0 alle 1.0arrow_forwardThe iron-iron carbide phase diagram. In the diagram, the letter L indicates that it is a liquid. Indicate what its components are. Temperature (°C) 1600 10 Composition (at% C) 15 25 1538°C -1493°C 8 1400 1200 1394°C y+L L 2500 1147°C y. Austenite 2.14 4.30 2000 1000 912°C y + Fe3C 800ㅏ 0.76 0.022 600 a, Ferrite a + Fe3C 400 0 (Fe) Composition (wt% C) 727°C 1500 Cementite (Fe3C) 1000 6 6.70 Temperature (°F)arrow_forward
- Part V. Choose which isomer would give the 1H-NMR spectrum below. Justify your reasoning by assigning important signals to the Corresponding protons of the correct molecule. A D on of of of H H 88 2 90 7.8 7.6 7.4 80 5 6 [ppm] 7.2 6.8 6.6 6.4 ō [ppm]arrow_forwardShow work with explanation. don't give Ai generated solutionarrow_forwardQ7. a. Draw the line-bond structure of the major product for the following reaction, if a reaction occurs, assume monohalogenation. b. Calculate the product ratios using the following information (hint: use the number of hydrogens in each category present to calculate the ratios). Chlorination: 1° Reactivity=1 2° Reactivity=4 Heat + Cl2 3° Reactivity=5arrow_forward
- Please correct answer and don't use hand rating and don't use Ai solutionarrow_forwardQ10: Alkane halogenation a. Give the name and structures of the five isomeric hexanes. Page 4 of 5 Chem 0310 Organic Chemistry 1 Recitations b. For each isomer, give all the free radical monochlorination and monobromination products that are structurally isomeric.arrow_forwardQ9. The insecticide DDT (in the box below) is useful in controlling mosquito populations and has low toxicity to humans, but is dangerous to birds and fish. Hoping to alleviate the dangers, little Johnny Whizbang, an aspiring chemist, proposes a new version of DDT ("Bromo-DDT") and shows his synthesis to his boss. Will Johnny Whizbang's synthesis work? Or will he be fired? Assume there is an excess of bromine and polybrominated products can be separated. Explain why. CH3 Br2, light CBR3 ok-ok Br Br Br Br CI "Bromo-DDT" CCl 3 DDT (dichlorodiphenyltrichloroethane) CIarrow_forward
- Differentiate the terms Monotectic, Eutectic, Eutectoid, Peritectic, Peritectoid.arrow_forwardQ5. Predict the organic product(s) for the following transformations. If no reaction will take place (or the reaction is not synthetically useful), write "N.R.". Determine what type of transition state is present for each reaction (think Hammond Postulate). I Br₂ CH3 F2, light CH3 Heat CH3 F₂ Heat Br2, light 12, light CH3 Cl2, lightarrow_forwarda. For the following indicated bonds, rank them in order of decreasing AH° for homolytic cleavage. Based on your answer, which bond would be most likely to break homolytically? (a) (c) H3C CH3 .CH3 CH3 CH3 (b) Page 1 of 5 Chem 0310 Organic Chemistry 1 Recitations b. Draw all the possible radical products for 2-methylbutane, and determine which bond is most likely to be broken.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY